156732-13-7

Basic information

• Product Name: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one
• Synonyms: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one;(S,Z)-5-AMINO-2-(DIBENZYLAMINO)-1,6-DIPHENYLHEX-4-EN-3-ONE,98%;(S,Z)-5-AMino-2-(dibenzylaMino)-1,6-diphenylhex-4-ene-3-one (DAH-II);(2S)-5-AMino-2-[bis(phenylMethyl)aMino]-1,6-diphenyl-4-hexen-3-one;(S)-2-AMino-5-(N,N-dibenzylaMino)-4-oxo-1,6-diphenylhex-2-ene;(S,Z)-5-AMino-2-(DibenzylaMino)-1,6-Diphenylhex-4-En-3-One (DAH-2);2-AMINO-5(S)-N,N-DIBENZYL AMINO-3-OXO-1,6-DIPHENYL HEX-2-ENE;4-Hexen-3-one,5-aMino-2-[bis(phenylMethyl)aMino]-1,6-diphenyl-, (2S)-
• CAS NO: 156732-13-7
• Molecular Formula: C32H32N2O
• Molecular Weight: 460.61
• EINECS: 1312995-182-4
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates
• Mol File: 156732-13-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 626.161 °C at 760 mmHg
• Flash Point: 332.49 °C
• Appearance: /
• Density: 1.137 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• PKA: 5.58±0.70(Predicted)
• CAS DataBase Reference: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(156732-13-7)
• EPA Substance Registry System: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(156732-13-7)

Safety Data

• Hazardous Substances Data: 156732-13-7(Hazardous Substances Data)

Usage

Description

(S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one is a light yellow crystalline solid that serves as an intermediate in the synthesis of Ritonavir, an antiretroviral medication used to treat HIV and AIDS.

Uses

Used in Pharmaceutical Industry:
(S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one is used as a chemical intermediate for the production of Ritonavir, an antiretroviral drug. Its role in the synthesis process is crucial for the development of medications that help combat HIV and AIDS, providing a vital contribution to the healthcare sector.
Used in Chemical Synthesis:
As a light yellow crystalline solid, (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one can also be utilized in various chemical synthesis processes, potentially leading to the creation of other valuable compounds and materials. Its unique structure and properties make it a versatile building block in the field of organic chemistry.

InChI:InChI=1/C32H32N2O/c33-30(21-26-13-5-1-6-14-26)23-32(35)31(22-27-15-7-2-8-16-27)34(24-28-17-9-3-10-18-28)25-29-19-11-4-12-20-29/h1-20,23,31H,21-22,24-25,33H2/b30-23-/t31-/m0/s1

Upstream product

• 156732-12-6 (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 75-05-8 acetonitrile 
• 63-91-2 L-phenylalanine 
• 100-44-7 benzyl chloride 

Downstream Products

• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 
• 156732-14-8 (2S,5S)-5-amino-2-dibenzylamino-3-oxo-1,6-diphenylhexane 
• 162849-93-6 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 192725-49-8 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane 

Relevant articles and documents

A convenient synthesis of enaminones using tandem acetonitrile condensation Grignard addition

Condensations of N,N-dibenzyl α-amino esters with the anion of acetonitrile followed by the addition of a Grignard reagent(proceed in excellent yields. This affords rapid access to the peptidomimetic precursor α-amino enaminones in one pot one the esters.

Preparation method of ritonavir and lopinavir intermediates

The invention discloses a preparation method of ritonavir and lopinavir intermediates. The method comprises the steps: using L-phenylalanine as a raw material to react with benzyl chloride in potassium carbonate and an alkaline aqueous solution to obtain N, N-dimethylformamide; condensing with acetonitrile under the action of sodium amide; carrying out addition reaction with benzyl magnesium chloride; sequentially reducing enamine and carbonyl by using sodium borohydride/methanesulfonic acid and sodium borohydride/trifluoroacetic acid reagents; obtaining a stereoselective product, namely, dibenzylamino-3-hydroxy-5-amino-1, 2, 4-triazole under the induction effect of a chiral inducer; the stereoselective product reacts with di-tert-butyl methyl dicarbonate in a potassium carbonate/tetrahydrofuran solution, ammonium formate and palladium/carbon are used for reduction debenzylation, and the intermediate BDH is obtained. The preparation method is high in stereoselectivity, the diastereomeric excess (de%) value of the chiral product is high, the reaction steps are short, the product yield is high and generated three wastes are few.

Method for synthesizing ritonavir intermediate

The invention relates to a method for synthesizing a ritonavir intermediate. The intermediate is (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. The method comprises the following steps: mixing L-phenylalanine, water and sodium hydroxide, adding benzyl chloride, adding heptane, washing the above obtained material with a methanol-water solution, and carrying out reduced pressure evaporation to obtain yellow oil benzyl 2-dibenzylamino-3-phenylpropionate; and dissolving the yellow oil in methyl tert-butyl ether under the protection of nitrogen, reacting the obtained solution with anhydrous acetonitrile, adding sodium hydride, stirring all above materials, slowly dropwise adding a Grignard reagent, cooling, adding anhydrous methanol for hydrolyzing superfluous sodium amide, allowing the obtained solution to stand for layering, extracting the obtained water layer with methyl tert-butyl ether, mixing oil layers, concentrating the obtained oil layer mixture, evaporating the obtained concentrate to obtain oil, adding anhydrous methanol, filtering the oil, and carrying out vacuum drying to obtain white powder which is the ritonavir intermediate (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. Compared with traditional technologies, the method provided by the invention has the advantages of reaction step simplification, reaction cost reduction, and reduction of use of toxic reagents.